TELAGLENASTAT

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Synonyms
Status
Molecule Category UNKNOWN
UNII U6CL98GLP4

Structure

InChI Key PRAAPINBUWJLGA-UHFFFAOYSA-N
Smiles O=C(Cc1cccc(OC(F)(F)F)c1)Nc1ccc(CCCCc2nnc(NC(=O)Cc3ccccn3)s2)nn1
InChI
InChI=1S/C26H24F3N7O3S/c27-26(28,29)39-20-9-5-6-17(14-20)15-22(37)31-21-12-11-18(33-34-21)7-1-2-10-24-35-36-25(40-24)32-23(38)16-19-8-3-4-13-30-19/h3-6,8-9,11-14H,1-2,7,10,15-16H2,(H,31,34,37)(H,32,36,38)

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H24F3N7O3S
Molecular Weight 571.59
AlogP 4.55
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 12.0
Polar Surface Area 131.88
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 40.0
Assay Description Organism Bioactivity Reference
Enzyme Assay-Time Dependence: Compounds were assessed for their ability to inhibit the enzymatic activity of a recombinant form of Glutaminase 1 (GAC) using a biochemical assay that couples the production of glutamate (liberated by GAC) to glutamate dehydrogenase (GDH) and measuring the change in absorbance for the reduction of NAD+ to NADH. Homo sapiens 5.0 nM
Inhibition of recombinant HIs-tagged human GAC (residue 72-603 aa) expressed in Escherichia coli after 10 mins using glutamine as substrate Homo sapiens 180.0 nM
Cytotoxicity against human MDA-MB-231 cells measured on 6th day by hemocytometry Homo sapiens 33.0 nM
Inhibition of human kidney type glutaminase (124 to 669 residues) using L-[3H]-glutamine as substrate after 45 mins by topcount method Homo sapiens 60.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -3.03 %
Inhibition of GAC (unknown origin) assessed as NADH formation using 10 mM glutamine as substrate preincubated for 60 mins Homo sapiens 5.0 nM
Inhibition of GAC (unknown origin) Homo sapiens 5.0 nM
Inhibition of human GLS1 assessed as reduction in glutamate production in presence of NADPH-dependent glutamate dehydrogenase by coupled biochemical assay Homo sapiens 30.0 nM
Binding affinity to human GLS1 expressed in Escherichia coli strain BL21 (DE3)pLysS by SPR assay Homo sapiens 92.0 nM
Inhibition of N-[2-[(3',6'-dihydroxy-1-oxo-spiro[isobenzofuran-3,9'-xanthene]-5-yl)carbamothioylamino]ethyl]-N'-[6-[4-[5-[[2-(2-pyridyl)acetyl]amino]-1,3,4-thiadiazol-2-yl]butyl]pyridazin-3-yl]pentanediamide binding to human GLS1 expressed in Escherichia coli strain BL21 (DE3)pLysS by fluorescence polarization binding assay Homo sapiens 110.0 nM
Inhibition of human GLS1 expressed in Escherichia coli strain BL21 (DE3)pLysS pre-incubated for 10 mins before glutamine addition and measured after 60 mins by bovine liver glutamate dehydrogenase based coupled enzyme assay Homo sapiens 38.0 nM
Antiproliferative activity against human HCT116 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Homo sapiens 60.0 nM
Antiproliferative activity against human MDA-MB-436 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Homo sapiens 520.0 nM
Inhibition of recombinant 6His-tagged GLS1 KGA isoform (unknown origin) (63 to 669 residues) expressed in Escherichia coli using glutamine as substrate preincubated for 15 mins followed by substrate addition and measured after 60 mins by amplex red staining-based horseradish peroxidase/glutamate oxidase coupled assay Homo sapiens 7.0 nM
Inhibition of GLS in human PC3 cells using glutamine as substrate measured after 6 hrs by amplex red staining-based horseradish peroxidase/glutamate oxidase coupled assay Homo sapiens 0.2 nM
Inhibition of human KGA preincubated for 15 to 30 mins followed by substrate addition and measured after 3 to 4 hrs by GDH-EZMTT reagent-based GDH coupled assay Homo sapiens 2.0 nM
Antiproliferative activity against human A549 cells after 5 days by EZMTT reagent-based assay Homo sapiens 40.0 nM
Antiproliferative activity against human Caki1 cells after 5 days by EZMTT reagent-based assay Homo sapiens 40.0 nM
Antiproliferative activity against human HCT116 cells after 5 days by EZMTT reagent-based assay Homo sapiens 28.0 nM
Antiproliferative activity against human MDA-MB-231met2 cells Homo sapiens 2.0 nM
Inhibition of GAC (unknown origin) Homo sapiens 20.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 9.08 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.78 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.11 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.11 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 %
Inhibition of human recombinant glutaminase assessed as reduction in glutamate production in presence of NADPH-dependent glutamate dehydrogenase preincubated 60 mins by coupled biochemical assay Homo sapiens 50.0 nM
Allosteric inhibition of human kidney glutaminase using [3H]-Glutamine as substrate in presence of inhibitor incubated for 45 mins by Perkin Elmer based assay Homo sapiens 50.0 nM
Antiproliferative activity against human A549 cells assessed as reduction in cell viability measured after 72 hrs by celltiter-fluor assay Homo sapiens 6.0 nM
Inhibition of recombinant human GLS1 using glutamine as substrate preincubated for 10 mins followed by substrate addition and measured after 20 mins by glutamate oxidase/horseradish peroxidase-coupled Amplex UltraRED reagent based fluorescence assay Homo sapiens 6.0 nM
Inhibition of recombinant human GLS1 expressed in Escherichia coli strain BL21 (DE3) preincubated for 10 mins before glutamine addition and measured after 60 mins by bovine liver glutamate dehydrogenase based coupled enzyme assay Homo sapiens 22.0 nM
Antiproliferative activity against human HCT116 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Homo sapiens 110.0 nM
Antiproliferative activity against human MDA-MB-436 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Homo sapiens 430.0 nM
Binding affinity to human GLS1 expressed in Escherichia coli strain BL21 (DE3) by ITC analysis Homo sapiens 105.0 nM
Inhibition of GLS1 (unknown origin) Homo sapiens 20.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL3639788
DrugBank DB15232
FDA SRS U6CL98GLP4
Guide to Pharmacology 9053
PDB 63J
PubChem 71577426
SureChEMBL SCHEMBL14987180
ZINC ZINC000169698697
CONTENTS